Upgrade: Guitar vs Amp
Would you buy a smart new guitar...
...or a new amp, should you have a sizeable amount of cash & would like to 'upgrade'?
I've talked to some people lately who are facing this snooker; they could acquire either item but not both. In this case, I'd urge you to consider your situation & assess your needs. You requirement to look at what you have; how pathetic are your amp & guitar, which is the greater culprit?
If you think you need a revision in tone, you should allot in a new amp. Simply put, a $50K guitar sounds pathetic through a fundamental practice unit, but a $500 guitar would have you smiling if you block it into the right amp (my right, isn't your right, do keep this in mind). I believe, before one buys a guitar, if it's within your financial means, get the one that you actually like, the one you'd keep on playing regardless of the countless pedal addition or the number of amps you PR it into. This way, future upgrading plans would mean your guitar is the least likely factor of your unhappiness.
From a personal standpoint, this is perhaps why the number of amps I own are limited as oppossed to the number of guitars; I'm very happy with what I hear from my Marshall & Hale and hearty Drive. The different guitars I plug into them provide a differentiated enjoyment of the same, likeable,...